2-(6-巯基己基)异吲哚-1,3-二酮 | 85847-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: 2-(6-巯基己基)异吲哚-1,3-二酮
• 英文名称: 2-(6-mercaptohexyl)isoindoline-1,3-dione
• 英文别名: N-(6-mercaptohexyl)phthalimide；6-phthalimidohexanethiol；2-(6-sulfanylhexyl)-2,3-dihydro-1H-isoindole-1,3-dione；2-(6-sulfanylhexyl)isoindole-1,3-dione
• CAS: 85847-47-8
• 化学式: C₁₄H₁₇NO₂S
• mdl: MFCD22905249
• 分子量: 263.36
• InChiKey: NUVFBSOIAXOTOJ-UHFFFAOYSA-N

物化性质

• 熔点：
  41-42 °C
• 沸点：
  404.8±28.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  38.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(6-巯基己基)异吲哚-1,3-二酮 在 palladium diacetate 、 potassium carbonate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 间氯过氧苯甲酸 、 锌 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Novel CDKs inhibitors for the treatment of solid tumour by simultaneously regulating the cell cycle and transcription control

  摘要：

  A novel series of cyclin-dependent kinases (CDKs) inhibitors, which play critical roles in the cell cycle control and regulation of cell transcription, were synthesised. A systematic study of enzymatic and cellular assays led to the identification of compound X22 with a nanomolar potency against CDK4 and CDK9 and potent antiproliferative activities against a panel of tumour cell lines. X22 could induce cell cycle arrest and cell apoptosis in cancer cell lines. X22 dose-dependently inhibits signalling pathways downstream of CDKs in cancer cells. In vivo antitumor activity assays, oral administration of X22 led to significant tumour regression in mouse model without obvious toxicity. Superior anti-cancer efficacy in vitro and in vivo of X22 demonstrated combined depletion of cell cycle and transcriptional CDK all contributed to antitumor activity. Taken together, concomitant inhibition of cell cycle and transcriptional CDK activities provided valuable guide for further structural optimisation.

  DOI：

  10.1080/14756366.2019.1705290
• 作为产物：
  描述：

  potassium phtalimide 在 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 15.25h， 生成 2-(6-巯基己基)异吲哚-1,3-二酮
  参考文献：
  名称：

  Synthesis and biological evaluation of sulforaphane derivatives as potential antitumor agents

  摘要：

  A series of sulforaphane derivatives were synthesized and evaluated in vitro for their cytotoxicity against five cancer cell lines (HepG2, A549, MCF-7, HCT-116 and SH-SY5Y). The pharmacological results showed that many of the derivatives displayed more potent cytotoxicity than sulforaphane (SFN). Furthermore, SFN and derivative 85 could induce cell cycle arrest at S or G2/M phase and cell apoptosis. SFN and 85 exhibited time- and dose-dependent activation on Nrf2 transcription factor, and 85 acted as a more potent Nrf2 inducer than SFN. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.045

文献信息

• Acheson, R. Morrin; Constable, Edwin C.; Wright, R. Gordon McR., Journal of Chemical Research, Miniprint, 1983, # 1, p. 101 - 132
  作者：Acheson, R. Morrin、Constable, Edwin C.、Wright, R. Gordon McR.、Taylor, Grahame M.

  DOI：——

  日期：——
• Total synthesis of racemic diptocarpidine and diptocarpiline
  作者：O. V. Tolstikova、A. G. Tolstikov、V. S. Shmakov、E. G. Galkin、I. B. Abdrakhmanov、S. F. Aripova

  DOI：10.1007/bf00597577

  日期：——
• Synthesis and biological evaluation of sulforaphane derivatives as potential antitumor agents
  作者：Kun Hu、Yan-jie Qi、Juan Zhao、He-fei Jiang、Xin Chen、Jie Ren

  DOI：10.1016/j.ejmech.2013.03.045

  日期：2013.6

  A series of sulforaphane derivatives were synthesized and evaluated in vitro for their cytotoxicity against five cancer cell lines (HepG2, A549, MCF-7, HCT-116 and SH-SY5Y). The pharmacological results showed that many of the derivatives displayed more potent cytotoxicity than sulforaphane (SFN). Furthermore, SFN and derivative 85 could induce cell cycle arrest at S or G2/M phase and cell apoptosis. SFN and 85 exhibited time- and dose-dependent activation on Nrf2 transcription factor, and 85 acted as a more potent Nrf2 inducer than SFN. (C) 2013 Elsevier Masson SAS. All rights reserved.
• ACHSON, R. M.;CONSTABLE, E. C.;WRIGHT, R. G. ,, MCR.;TAYLOR, G. N., J. CHEM. RES. MICROFICHE, 1983, N 1, 2-3
  作者：ACHSON, R. M.、CONSTABLE, E. C.、WRIGHT, R. G. ,, MCR.、TAYLOR, G. N.

  DOI：——

  日期：——
• TOLSTIKOVA, O. V.;TOLSTIKOV, A. G.;SHMAKOV, V. S.;GALKIN, E. G.;ABDRAXMAN+, XIMIYA PRIROD. SOED.,(1988) N 1, 76-82
  作者：TOLSTIKOVA, O. V.、TOLSTIKOV, A. G.、SHMAKOV, V. S.、GALKIN, E. G.、ABDRAXMAN+

  DOI：——

  日期：——